1. Beach Boys, "Sloop John B"
This 1966 track from the infallible Pet Sounds album was inspired by a few old traditional songs about rowdy, true-blue sea men and a 1958 Kingston Trio recording "The Wreck of the John B." suggested by guitarist Al Jardine. It's a pretty unglamorous look at life on the water: catching "the fits," getting so drunk they get into fights and break into each others' bunks...we'd wanna go home too.
2. Duran Duran, "Rio"
The lyrics have nothing to do with sailing, but since when do you listen to Duran Duran for its lyrics? Here, it's all about the music video, where the entire band speeds around on a luxury yacht (symbolizing 80s excess, of course), getting goofed over and over by a body-painted Patrick Nagel painting come to life. The cherry on top? The saxophone solo, both in the song and on the video, which gives the one from "Careless Whisper" a serious run for its money.
3. Cream, "Tales of Brave Ulysses"
Obviously inspired by history's OG sailor, Ulysses, the lyrics to this psychedelic masterpiece were also influenced by Martin Sharp's, who wrote them, recent return from a trip to idyllic Ibiza, back to the UK. They totally belong framed on a wall, written in embroidery, don't you think? Making the song even better is the fact that Clapton had discovered the wah wah pedal only a day before "Tales" was recorded.
4. Looking Glass, "Brandy"
One of the best one-hit-wonders ever, this is a sad song in disguise (and karaoke barnburner) about a bartendress hopelessly in love with a sea-faring man. Ladies, take note, and steer clear. The same song could be written about traveling salesmen, touring musicians, travel writers, flight attendants, or any member of the armed services.
5. Otis Redding, "Dock of the Bay"
In my opinion one of the finest songs ever written, sung and whistled, this stone-cold classic was written by Redding on a houseboat in Sausalito just after his legendary stint at the Monterey Pop Festival in 1967. Its slow groove and buoyant bassline captures the ebb and flow of the Bay, and the ships criss-crossing its surface day in and day out. The lyrics capture the loneliness of life on the road as a musician, the silent moments in between the glory of playing of shows. It was and still feels like something this soul superstar would write in his journal, and every time I listen to it, I feel like I'm reading the secret thoughts of a long-dead relative I always wanted to know but never did.